N-[2-(1,2,3,5,6,7-hexahydropyrrolizin-8-yl)ethyl]-2-nitroaniline → N-[2-(1-Azabicyclo[3.3.0]octan-5-yl)ethyl]-2-nitroaniline(maleate)

HRID 260935Notes

Reaction equation

HRID 260935 reaction equation
[N:1]12[CH2:8][CH2:7][CH2:6][C:5]1([CH2:9][CH2:10][NH:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[N+:18]([O-:20])=[O:19])[CH2:4][CH2:3][CH2:2]2.[C:21]([OH:28])(=[O:27])/[CH:22]=[CH:23]\[C:24]([OH:26])=[O:25]>C(O)C>[C:21]([OH:28])(=[O:27])/[CH:22]=[CH:23]\[C:24]([OH:26])=[O:25].[N:1]12[CH2:8][CH2:7][CH2:6][C:5]1([CH2:9][CH2:10][NH:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[N+:18]([O-:20])=[O:19])[CH2:4][CH2:3][CH2:2]2

Participants

4

Reactant 2

HCID 178115N-[2-(1,2,3,5,6,7-hexahydropyrrolizin-8-yl)ethyl]-2-nitroanilineHCID 444266Maleic Acid

Product 1

HCID 67740001N-[2-(1-Azabicyclo[3.3.0]octan-5-yl)ethyl]-2-nitroaniline(maleate)Yield 791.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A mixture of N-[2-(1-azabicyclo[3.3.0]octan-5-yl)ethyl]-2-nitroaniline (200 mg, 725 μmol) obtained by Example 23 in ethanol (10 Ml) and maleic acid (84.2 mg, 72 μmol) in ethanol (10 ml) was concentrated until its volume becomes 3 ml and left to stand to afford the desired salt (223 mg, 78.6%).

Workup

  1. concentrationwas concentrated until its volume
  2. waitleft

Sources & evidence

ORD record
ord-4f6098d0403642a2989057b14f22a948
Source dataset
uspto-grants-1996_06
Patent number
US05530138

Reaction notes

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